Stereoselective Transformation of 2H-1, 4-Oxazin-2-ones into 2,(2), 5, 5-Tri-and Tetrasubstituted Analogues of cis-5-Hydroxy-2-piperidinemethanol and cis-5-Hydroxy- …

X Wu, K Dubois, J Rogiers, S Toppet, F Compernolle…

Index: Wu, Xiujuan; Dubois, Kristof; Rogiers, Joeri; Toppet, Suzanne; Compernolle, Frans; Hoornaert, Georges J. Tetrahedron, 2000 , vol. 56, # 19 p. 3043 - 3051

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Citation Number: 19

Abstract

2,(2), 5, 5-Tri-and tetrasubstituted analogues of 5-hydroxy-2-piperidinemethanol and 5- hydroxy-6-oxo-2-piperidinecarboxylic acid have been prepared via Diels–Alder reaction of 3- substituted 2H-1, 4-oxazin-2-ones with ethene followed by functional group transformation of the resulting imidoyl chloride and lactone groups. Some of the 2-piperidinemethanol products are converted further into potential substance P antagonists.